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Is a Freelance Career Right for You?

Last year, I left my job as a marketing professional in higher education and took a career detour (I may have mentioned this). I quit my job of six years — a field I had about 15 years of experience in — and gave myself a new title: freelance writer. Being a freelance writer seemed to be the answer to many problems. It took my career in the direction I wanted to go (writing), while giving me the flexible schedule I had craved since my daughter was born (freelance). But striking out on my own was unlike any choice I had ever made. I was starting a business after being employed by someone else since college, which was scary and unchartered territory.

Like with most life choices, I consulted the internet. I read lots of freelance websites, and many of them were helpful. But I could never find information about of what type of person is a successful freelancer — or at least, what kind of traits help a person manage the quirks of a freelance career. In fact, I even asked this question in a freelance forum run by a well-known writer, and received a somewhat rude response along the lines of “how would [she] know,” which was, you know… not helpful.

So I’m writing that post myself. After a year of being a freelance writer, I’ve compiled a few… I guess I’d call them life or coping skills that seem to be critical to not only actually building a career, but managing the vast differences between being employed by someone else and being self-employed.

You can handle uncertainty — lots of uncertainty.

Being a freelancer, especially a new freelancer, means your income is inconsistent, the number of hours you’re actually working and getting paid is inconsistent, how much you’re charging might even be inconsistent… basically there’s a lot of inconsistency. For me, the most nerve-racking part of those inconsistencies was the money part.

If you’re comfortable hanging out in that uncertainty, at least for awhile (at least one year, maybe two), then a freelance career might be a great choice for you. I find this is only palatable if you can reasonably live without a second income, i.e., you have someone bringing home a paycheck that covers all of the bases: mortgage, bills, groceries, and so on. But even if you do have this, and we did, going from two full-time and steady incomes to one plus whatever you make freelancing, which can vary significantly month to month, can be a huge, huge shock to the budget and the system.

You don’t mind being alone.

When you work freelance, you spend a lot of time working alone. There’s no one down the hall to chat with, and you’re not in the mix with any office gossip (for better or worse). Sure, head to the coffeeshop, but chances are you’re just going to sit there by yourself. Being a freelancer is often very quiet. If you’re a person who lives in your own head, this can be dangerous. I didn’t have too much of a problem being alone, but when I ended up back in an office environment, I was practically giddy to have people around.

You are able to set boundaries about when and how your work.

Doesn’t a freelance career sound like the answer to all work-life balance issues? You can work when you want and how much you want, on projects that interest you, etc. The flip side is that being a freelancer means your start time and your stop time are entirely up to you. I often felt like I could and maybe should be working around the clock. Without the artificial boundaries of 9-to-5, stopping work (however work was being defined) was sometimes hard. For me, turning off the to-do list was difficult even during the evenings or to stop for an hour mid-day for some of that “balance” I was so hoping for.

You are self-disciplined and self-directed.

If you’re not self-disciplined and self-directed, a freelance career is not for you. I am definitely disciplined enough (I think), and I’m self-directed when I have a project for a client, but the business of setting up a thriving freelance career means that you have to market yourself (more on that in a minute). This part was particularly hard for me. I struggled to figure out what direction I should take my writing career in (Do I pitch publications, work on the blog, or focus on marketing copywriting? Do I sell myself to a particular industry or will I take whatever I can get? There were a lot of options/questions.) There is a literally endless and mostly undefined list of things a freelancer could be doing to forward her business goals. I often felt stuck in the business of being a freelancer, unsure what would be the most bang for my time-is-money buck.

You’re comfortable with self-promotion.

When you’re working for yourself, you have to market your services, which ultimately means that you have to market yourself. Now, there are totally freelancing writing jobs that you can get without marketing yourself. I definitely got jobs by simply applying for them — the About.com gig is a good example of that. But, my best gigs came about from networking and reaching out to contacts I already had. One great gig I got was with a university, which came about from a letter of inquiry I wrote to a woman I interviewed with a year an a half earlier. Another came from someone I met in a running group who ended up being a VP at a higher education marketing agency. Writing that email to the woman I barely knew was hard. Talking to the VP about what I did and what kind of work I was looking for, and straight up asking her to pass along my resume to the people who make these decisions was hard. For me, self-promotion was… unpleasant — it felt like I was constantly asking for favors — but it was doable, and I got better at it as time went on.

You’re capable of advocating for a fair rate in exchange for your services.

So this isn’t a personality trait, exactly, but I found that advocating for a fair rate was extraordinarily difficult and very, very important. First of all, it’s hard to find good information about what exactly you should be charging, and freelance writing rates are literally all over the board. There are people making well below the minimum wage writing for Upwork and other content mill-type sites. There are people charging over $100 an hour for copywriting services. Most publications typically have a set rate that they pay — blogs, if they pay at all, can pay as low as $25 or $50 with online media sites like Jezebel clocking in at $250. Consumer magazines typically pay more, trade magazines often higher still. In the interest of getting the work I desperately felt I needed, I had trouble asking for what truly deserved. I worked in exchange for services sometimes, my rates were all over the map, and I took whatever I could get.

Here’s the good news: I got better at this, and with a few exceptions, by late summer 2015, I had set a rate of $40/hour for copywriting services, which cut me out of the running for a lot of local and smaller businesses looking for writing services. That, I learned, was OK. But here’s the bad news: As I saw very clearly this week while looking at a freelance writer’s proposal that I should have been charging more.

You don’t mind working with minimal direction and appreciation.

I’ll give myself this much — Working with minimal direction, dealing with gray areas, and coping with missing information about what a client or employer actually wants when it comes to copywriting, I can easily live in this space. I have a sense of when to push for more direction and when not to, and my instincts on how to approach something totally undefined are often close to spot on. I don’t know how I got here, but it’s definitely one of my strengths. Writing for media outlets, I would say this is less true, but I’m comfortable with a swing and a miss, which might just be a byproduct of age and experience. The bottom line: When you’re a freelancer, no one is holding your hand, and you can’t walk down the hall to get clarification. You have to have the confidence in your ability to just move forward and get the work done.

As for appreciation, as a freelancer, you will not find an overabundance of it. You’ll have clients who are grateful and clients who like you, but you’re not really part of the team. You’re the hired help, quite literally, and the whole point of being a good freelancer — IMHO — is that you can quickly do the work with minimal direction and without being coddled. That’s what they are paying you for.

You’re patient.

Taking a sharp career turn to freelancer often means playing the long game when it comes to building a reputation, a client base, and an income. That marketing and self-promotion I did? I sent the email to the woman at the university in February or March. In October, I was contacted by another woman in her division — my resume had been passed along. The running group VP? I gave her my information in July. I heard from that agency in October too.

It takes awhile. Since the beginning of February, I’ve been contacted by another higher education institution and another agency, both because I had contacts who knew me, with gigs that would have paid well. I had to say no. But, it drove home the point: It takes some time to really establish yourself as a freelancer. If I would have stuck it out, I likely would have had a lot more options today than I had this time last year. But the thought of a steady paycheck and boundaries of a normal work day were too good to pass up after a year of uncertainty.

2 thoughts on “Is a Freelance Career Right for You?”

While indulging in some ridiculous television a few weeks ago, one of those crazy sharks on Shark Tank said “If you want a work/life balance, do not start your own company.” It is so very true! While I think eventually you can get to a point where you have more balance, that feeling of always looking for your next paying gig never really goes away. Perhaps that feeling is what propels people to success, but it is also what keeps them awake at night. For now, I would pick a steady check and regular hours over the uncertainty as well.

I think a lot of these can be applied to a remote working situation. This particularly hit me: I didn’t have too much of a problem being alone, but when I ended up back in an office environment, I was practically giddy to have people around.

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